Chiefly Product
Practical, direct, and clarity-building insights on Product, technology, AI, data, leadership, strategy, and transformation. Written by a portfolio CPO working in private equity. Real-world playbooks, battle-tested frameworks, and sharp lessons learned.
- Indexed issues, last 90 days
- 13
- Latest publication
- Sep 29, 2026
- Audience
- Checking…
- Earliest in this view
- Sep 1, 2026
Latest issues
Product is Dead (opens the original)
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<img alt="" class="sizing-normal" height="900" src="https://substackcdn.com/image/fetch/$s_!xNUO!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F32ba8b0e-3700-4eff-9358-3910b59288ab_1260x900.png"
Sunday Drop #64 - Things That Are Becoming Harder to Explain to a Board (opens the original)
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There are good reasons to take things to a Board. Strategy, capital allocation, risk, major changes in direction, and decisions where the consequences extend well beyond the normal remit of the executive team all belong there. Boards exist to provide governance, oversight, challenge, and, when required, approval.And then there are things which, increasingly, I’m not sure should require quite so much explaining.I’ve spent a reasonable amount of my working life somewhere between product teams, exe
What’s Your Personal Disaster Recovery Plan? (opens the original)
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I had dinner with two friends this week. They are two of the smartest and most impressive business leaders I know, and neither could be remotely described as melodramatic, prone to catastrophising, or particularly interested in conspiracy theories.And yet, by the end of dinner, we were effectively war gaming.We talked about what might happen if there were a serious cyberattack on UK infrastructure, whether the West is already on something approaching a war footing, and what an escalation might a
Nine Questions I Keep Hearing Right Now (opens the original)
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One of the privileges of working across multiple companies, sectors, investors, and leadership teams is pattern recognition. Different businesses have different problems, of course, but every so often the same questions start appearing in completely different rooms.These are the ones I keep hearing right now.<a class="image-link image2 is-viewable-img" href="https://images.unsplash.com/photo-1560036043-1a6b17791807?crop=entropy&cs=tinysrgb&fit=max&fm=jpg&ixid=M3wzMDAzMzh8MHwxfHNlYXJjaHw0MHx8cGF0
Sunday Drop #63 - Switching Modes (opens the original)
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<img alt="white bridge over the river" class="sizing-normal" height="710" src="https://substackcdn.com/image/fetch/$s_!rxmp!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fbdc157e7-b598-475f-bc2
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